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Chilmark Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In one month
Nov 14 - Nov 16
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11

Vacation Rentals in Chilmark

Private beach nearby, beach bar
The Club at New Seabury
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (336)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
The Club at New Seabury
Exterior detail
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
10.0 out of 10, Exceptional, (35)
"The location was a perfect fit for our needs. "
The price is ￥20,373
￥144,738 total
includes taxes & fees
Oct 20 - Oct 21
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Outdoor dining
Newly Renovated Martha's Vineyard Vacation Rental!
Newly Renovated Martha's Vineyard Vacation Rental!
9.6 out of 10, Exceptional, (46)
"Stay was nice, property is very clean and in close distance to most everything. Just wish they had made the lack of towels and linens more obvious in the listing. "
The price is ￥30,559
￥93,976 total
includes taxes & fees
Oct 17 - Oct 18
Newly Renovated Martha's Vineyard Vacation Rental!
Exterior
Partial Ocean View Studio w/ Private Deck (308)
Partial Ocean View Studio w/ Private Deck (308)
10.0 out of 10, Exceptional, (1)
"Room was in a great location close to the beach. Very clean, nice deck, right across from Vineyard Sound. Really enjoyed our stay."
The price is ￥20,441
￥25,735 total
includes taxes & fees
Nov 12 - Nov 13
Partial Ocean View Studio w/ Private Deck (308)
Property grounds
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
8.6 out of 10, Excellent, (87)
"Loved the neighborhood and proximity to the beach and marketplace. Cute space, host was very responsive. Would stay again"
The price is ￥45,273
￥93,786 total
includes taxes & fees
Oct 24 - Oct 25
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Beach nearby
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
8.2 out of 10, Very Good, (24)
"So turn key and perfect for Month, Joy is an exceptional host and I’d recommend her place anytime"
The price is ￥12,073
￥26,772 total
includes taxes & fees
Nov 13 - Nov 14
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
TV, fireplace, books
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
The price is ￥26,409
￥101,141 total
includes taxes & fees
Oct 24 - Oct 25
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Indoor pool, outdoor pool, sun loungers
Sea Mist Resort
Sea Mist Resort
3.0 star property
8.6 out of 10, Excellent, (138)
"Just there for one night but very enjoyable stay."
The price is ￥24,606
￥28,162 total
includes taxes & fees
Nov 7 - Nov 8
Sea Mist Resort
Exterior
King Room w/ Partial Ocean View Above Restaurant (203)
King Room w/ Partial Ocean View Above Restaurant (203)
The price is ￥20,441
￥25,735 total
includes taxes & fees
Nov 16 - Nov 17
King Room w/ Partial Ocean View Above Restaurant (203)
Interior
Charming studio in tranquil Falmouth with AC
Charming studio in tranquil Falmouth with AC
The price is ￥18,109
￥28,499 total
includes taxes & fees
Nov 13 - Nov 14
Charming studio in tranquil Falmouth with AC
Fridge, microwave, oven, stovetop
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (203)
"Loved this spot. So easy to get to downtown and Surf Beach. It was fabulous and clean!"
The price is ￥27,164
￥78,241 total
includes taxes & fees
Nov 16 - Nov 17
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Pool
Great Harbors Summer Home
Great Harbors Summer Home
The price is ￥66,796
￥169,582 total
includes taxes & fees
Nov 8 - Nov 9
Great Harbors Summer Home
Game room
Spring Escape in Hatchville – Sleeps 6 + Dogs!
Spring Escape in Hatchville – Sleeps 6 + Dogs!
10.0 out of 10, Exceptional, (11)
"The house is very nice and clean and Brian was extremely communicative and flexible with a late checkout. Would definitely stay again"
The price is ￥43,721
￥111,718 total
includes taxes & fees
Oct 18 - Oct 19
Spring Escape in Hatchville – Sleeps 6 + Dogs!
Smart TV
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
9.4 out of 10, Exceptional, (88)
"The location of this property cannot be beat! Our second time staying here."
The price is ￥45,273
￥80,912 total
includes taxes & fees
Nov 12 - Nov 13
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Terrace/patio
The Seashell Cove - Martha's Vineyard
The Seashell Cove - Martha's Vineyard
9.8 out of 10, Exceptional, (23)
"Property was perfectly kept and very comfortable. "
The price is ￥54,652
￥108,526 total
includes taxes & fees
Oct 19 - Oct 20
The Seashell Cove - Martha's Vineyard
Fridge, microwave, oven, stovetop
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
10.0 out of 10, Exceptional, (15)
"The house is beautiful and conveniently located. The host, Melissa, was accessible and super helpful. We thoroughly enjoyed our time here and hope to be back in the future."
The price is ￥78,473
￥167,555 total
includes taxes & fees
Oct 18 - Oct 19
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Fridge, microwave, oven, stovetop
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
10.0 out of 10, Exceptional, (7)
"Nice house! Great area. Close to nice beach !"
The price is ￥80,884
￥154,427 total
includes taxes & fees
Oct 21 - Oct 22
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
5 bedrooms, desk, iron/ironing board, travel crib
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Coastal chic meets French Provençal in this newly renovated oceanfront home.
10.0 out of 10, Exceptional, (87)
"Great stay! "
The price is ￥85,393
￥189,992 total
includes taxes & fees
Oct 27 - Oct 28
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
The price is ￥83,001
￥182,896 total
includes taxes & fees
Oct 23 - Oct 24
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Terrace/patio
Partial Ocean View Studio with Large Private Deck (307)
Partial Ocean View Studio with Large Private Deck (307)
10.0 out of 10, Exceptional, (1)
The price is ￥20,441
￥25,735 total
includes taxes & fees
Nov 3 - Nov 4
Partial Ocean View Studio with Large Private Deck (307)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chilmark Hotel Reviews

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Clean, safe, friendly, and a.good value."
Michael 1-night trip
Posted 3 days ago
Vineyard Harbor Motel - Private Beach

Find out more about Chilmark

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Frequently asked questions

Can I find vacation rentals in Chilmark?

Yes, there are vacation rentals in Chilmark near Chilmark Chocolates, or you can select a more secluded option if you're looking for extra privacy while you relax. Chilmark is known for its beaches and wineries. Make sure you have time to check out the festivals and local tours during your trip.

What are some of the best vacation rentals that Chilmark has to offer?

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub: This vacation home near Chilmark is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Chilmark?

Choose from 75 Expedia vacation rentals in Chilmark for a memorable vacation.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Menemsha Beach and Lucy Vincent Beach are a couple of great spots to enjoy the outdoors. While here, Chilmark Town Hall and Chilmark Public Library are other places worth a visit.

What’s a vacation rental in Chilmark like?

A vacation rental is a private property where you can stay for a long or short time in Chilmark. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.